期刊
ACS CATALYSIS
卷 5, 期 5, 页码 2826-2831出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b00311
关键词
alpha-azidation; 1,5-H shift; trifluoromethylation; gamma-lactam; spirobenzofuranone-lactam
资金
- National Natural Science Foundation of China [21302088, 21302087]
- South University of Science and Technology of China
The first unprecedented one-pot domino strategy toward diverse CF3-containing gamma-lactam and spirobenzofuranone-lactam scaffolds of antibacterial armeniaspirole from readily available acyclic precursors was developed. The key point of this transformation was the concurrent incorporation of CF3 and azide into the alkene and remote carbonyl alpha-C-H position via carbonyl-stabilized radical intermediate triggered by alkene trifluoromethylation via a 1,5-H shift in a highly controlled site-selective manner. Furthermore, gram-scale synthesis and synthetic applicability of these compounds proved suitable.
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